1-Bromooctane → HCID 22242474, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-hydroxy-1-(4-hydroxyphenyl)-2-methyl-1-propanone (10 g, 55.5 mmol) in dimethyl sulfoxide (DMSO) (125 ml) is added in the course of 1 hour at room temperature (RT), under argon, to a suspension of NaH (2.66 g, 61 mmol, 1.1 eq; 55–60% in oil, washed with hexane) in DMSO (40 ml). The mixture is stirred for 15 minutes at RT and for 15 minutes at from 35 to 40° C. A solution of 1-bromooctane (11.79 g, 61 mmol) in DMSO (10 ml) is added in the course of 15 minutes and the mixture is heated at 190° C. for 18 hours. The solution is poured onto ice and the resulting mixture is extracted with tert-butyl methyl ether (TBME). The organic phases are dried with MgSO4. After filtration and removal of the solvent by evaporation, the compound is obtained in the form of an oil. Flash chromatography yields 2-hydroxy-2-methyl-1-(4-octyloxy-phenyl)-propan-1-one (13.9 g, 85%) in the form of a yellow oil and 2-methyl-2-octyloxy-1-(4-octyloxy-phenyl)-propan-1-one (1.1 g; 5%) in the form of a yellow oil.

Provenance & Evidence